p-Anisoyl chloride → Methyl 4-[4-(4-methoxybenzoyl)phenoxy]butyrate

HRID 893409Notes

Reaction equation

HRID 893409 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.[O:16]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCCl>[CH3:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:18][CH:19]=2)=[O:12])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 568131Methyl 4-phenoxybutanoateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 14460992Methyl 4-[4-(4-methoxybenzoyl)phenoxy]butyrate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

25.6 g of anhydrous aluminum trichloride are suspended in 64 ml of 1,2-dichloroethane, and 28.6 g of 4-methoxybenzoyl chloride are added. Then, while stirring vigorously, 31 g of methyl 4-phenoxybutyrate are slowly added. The reaction mixture is subsequently stirred at 50° C. for 4 hours, allowed to cool and poured into ice-water. The oily organic layer and the aqueous phase are separated, the organic phase is washed with water, and a little methanol is added to induce crystallization. The product which has separated out is filtered off with suction and recrystallized from ethyl acetate.

Workup

  1. stirringThe reaction mixture is subsequently stirred at 50° C. for 4 hours
  2. temperatureto cool
  3. customThe oily organic layer and the aqueous phase are separated
  4. washthe organic phase is washed with water
  5. additiona little methanol is added
  6. customcrystallization
  7. customThe product which has separated out
  8. filtrationis filtered off with suction
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-326ace191a524ac0ab1096842660e376
Source dataset
uspto-grants-1992_06
Patent number
US05124478

Reaction notes

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